Should you ever convince someone not to quit?

As a manager, it’s hard to hear that someone wants to leave your company. The good news is this doesn’t always have to be a bad conversation. Perhaps they’ve found a great opportunity and you’re happy to have been a stepping stone on a great journey.

But sometimes a person is leaving because of issues that were within your control, issues that you failed to manage. While it should never come as a shock, it may be tempting to try and make them stay.

As I’m going to talk about in this article, sometimes this is the right thing to do. However I will add a big caveat upfront that once someone has decided to leave, even if you convince them to stay, they will inevitably leave at some point in the future. They’ve already crossed the bridge mentally, which makes it a lot easier to do the second time.

They’ve fired you so admit your mistakes

If you can acknowledge that you’ve made mistakes then you may be able to convince them to stay. They may not be leaving for the right reasons or they don’t have all the information to make an informed decision. Whatever the reason, if you honestly believe you made a mistake and you can engage them to help you fix it then you may have a chance.

Perhaps you haven’t given them the support they need or there’s a systemic issue that you failed to see. In these circumstances the first step is acknowledging that you didn’t do a good job understanding what they needed, or in explaining the opportunities that were available to them.

The next step is to outline exactly what you’re going to do about it and asking them to stay. This will only work if the company recognizes its mistake and takes responsibility for fixing it. Rather than focusing in on tactical things, like money, explore the systemic issues that got you to this point and amend those.

As the manager, it’s entirely on you to stick to your word. The individual has already done their bit when they fired you.

You rarely get two bites of this cherry

I know from experience that you don’t get two chances. When I first tried to leave Rising Sun Pictures, I felt that I’d reached a point where I’d taken all I could from the role. I was young and wanted to try other things. When I spoke to the founders, they outlined some opportunities they had planned to give me and offered to accelerate these. They followed through and shortly after, I became the general manager and happily stayed for another five years.

The next time I decided to leave it was for different reasons. It wasn’t an easy decision, but I felt that I was ready for something new. Once again they offered me a huge opportunity to try and convince me to stay, but I knew it was time for me to leave. It was a difficult decision to make and explain to them, but it was something I had to do.

When people at Culture Amp tell me that they’re thinking of leaving, I often tell this story. They’re often feeling incredibly stressed and hearing this helps validate their emotions and calms them down.

It’s only human to feel surprised when someone wants to leave, but it’s important not to come across that way. It’s okay for people to feel what they do. The key is helping them understand why they’re having these thoughts and supporting them to make the right choice. It can be a really powerful framing point, and it's an important part of their journey.

Money is never a good enough reason to stay

It’s never useful to try and engage a person to stay if all they ask for is more money. If this is the case you’ve already lost the battle because they’ve reduced their decision down to a purely monetary transaction.

If you do match their salary they’ll be gone within six months when someone else increases that number.

It’s not necessary, or appropriate, to try and stop everyone who wants to leave your organization. In a healthy organization, perhaps half the people that choose to leave are actually doing so for the right reasons. Even if they’re leaving you in the lurch, it’s important to consider the long-term benefits from their point of view. Trying to convince someone to stay to solve your own short-term pain isn’t helping them.

But if managers can enter into conversations that are open and productive, they can be beneficial for both the broader organization and the individual involved. At the end of the day, the individual may still feel like there is a mismatch and it’s time for them to leave. While you have to let them go, both of you may learn something in the process.